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Holiday Homes in The Berkshires
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Our top choices for The Berkshires holiday homes
Holiday Home in Great Barrington
Home in Great Barrington9.8 out of 10, Exceptional, (26)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
Cameron M.
The price is €224
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Home in Sherwood Forest
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is €325
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Sherwood Forest
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
James D.
The price is €344
includes taxes & fees
8 Jan - 9 Jan 2026
Holiday Home in Florida
Florida Mountain Log Cabin10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
Tristan e.
The price is €318
includes taxes & fees
13 Jan - 14 Jan 2026
Holiday Home in Pittsfield
3-bedroom house in beautiful Berkshires, close to amenities!The price is €277
includes taxes & fees
12 Jan - 13 Jan 2026
Holiday Home in Sheffield
Cheerful 3-bedroom cottage with woodstove10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
Kelly R.
The price is €437
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Home in Great Barrington
Family Ski Getaway in the Berkshires9.4 out of 10, Exceptional, (6)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
Kathy C.
The price is €260
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Home in Hancock
Comfortable Berkshires retreat on mtn resort, SISO9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
Javier
The price is €640
includes taxes & fees
3 Jan - 4 Jan 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top The Berkshires Hotel Reviews
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
Find out more about The Berkshires
The Berkshires Holiday Homes information
Number of reviews | 277 |
|---|---|
Accommodation | 327 Holiday Homes |
Lowest Price | €175 |
Highest Price | €1,520 |
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